ePrints

Elucidating Chiral Resolution of Aromatic Amino Acids Using Glycopeptide Selectors: A Combined Molecular Docking and Chromatographic Study

Lookup NU author(s): Dr Jie ZhangORCiD

Downloads

• Published version [.pdf]

Licence

This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

© 2024 by the authors.An asymmetric synthesis is a favorable approach for obtaining enantiomerically pure substances, but racemic resolution remains an efficient strategy. This study aims to elucidate the chiral resolution of aromatic amino acids and their elution order using glycopeptides as chiral selectors through molecular docking analysis. Chiral separation experiments were conducted using Vancomycin as a chiral additive in the mobile phase (CMPA) at various concentrations, coupled with an achiral amino column as the stationary phase. The Autodock Vina 1.1.2 software was employed to perform molecular docking simulations between each enantiomer (ligand) and Vancomycin (receptor) to evaluate binding affinities, demonstrate enantiomeric resolution feasibility, and elucidate chiral recognition mechanisms. Utilizing Vancomycin as CMPA at a concentration of 1.5 mM enabled the separation of tryptophan enantiomers with a resolution of 3.98 and tyrosine enantiomers with a resolution of 2.97. However, a poor chiral resolution was observed for phenylalanine and phenylglycine. Molecular docking analysis was employed to elucidate the lack of separation and elution order for tryptophan and tyrosine enantiomers. By calculating the binding energy, docking results were found to be in good agreement with experimental findings, providing insights into the underlying mechanisms governing chiral recognition in this system and the interaction sites. This comprehensive approach clarifies the complex relationship between chiral discrimination and molecular architecture, offering valuable information for creating and improving chiral separation protocols.

Publication metadata

Author(s): Gherdaoui D, Yahoum MM, Toumi S, Lekmine S, Lefnaoui S, Benslama O, Bouallouche R, Tahraoui H, Ola MS, Ali A, Zhang J, Amrane A

Publication type: Article

Publication status: Published

Journal: International Journal of Molecular Sciences

Year: 2024

Volume: 25

Issue: 16

Print publication date: 02/08/2024

Online publication date: 22/08/2024

Acceptance date: 20/08/2024

Date deposited: 10/09/2024

ISSN (print): 1661-6596

ISSN (electronic): 1422-0067

Publisher: Multidisciplinary Digital Publishing Institute (MDPI)

URL: https://doi.org/10.3390/ijms25169120

DOI: 10.3390/ijms25169120

Data Access Statement: Data are contained within the article.

PubMed id: 39201804

Altmetrics

Funding

Share